The Jai Journal

Entry // September 28th, 2024

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Why do I feel guilty whenever I’m not working?

This entry is a letter to myself. For the times I fall victim to my work and feel guilty for taking time off.

It’s a topic that i’ve heard from hundreds of high performing people.

“We work so hard to the extent that, when we finally take a little break from work—we have no idea how to rest and relax.” - Vizi Andrei.

There doesn’t seem to be a clear solution… or so you think.

A few years ago I spent a month in the USA with 2 friends. At the time I led a team of 13 people in a creative agency and they were mostly self-sufficient. It was the first time I’d been away since I started the business, so they were eager to prove they could sail the ship without me.

And for the most part, it did.

I spent the first week of the trip in Minneapolis (random, I know) for Gary Vee’s NFT conference. Despite being jetlagged and missing out on all the parties and networking because we were falling asleep at 4pm, I was feeling pretty good.

Then, New York City.

We stayed in a shoebox hotel room, 3 of us sharing 2 beds pushed together. I remember waking up to a wet floor because of the condensation of 3 dudes breathing throughout the night. We weren’t allowed to open a window as it was a health risk apparently. All part of the experience, I told myself.

The city was cool, but I was anxious 24/7.

Any moment I had spare I spent in the hotel lobby trying to work. Putting out client fires. Trying to make time for my girlfriend with a 12 hour time difference.

I was in one of the most inspiring cities in the world, yet I was miserable. Not even Central Park could pull me out of my head for more than a few minutes.

Then, 2 weeks cruising down the Californian coast. Similar feeling.

The trip was booked because we wanted to network, think bigger and get some time away from work. Yet I found myself staying in… to work. What the heck?

After that trip the cycle repeated itself for years. Taking time off was really only a less-productive work week. My skin suffered. My relationships suffered. I was a workaholic in denial.

Today, I work very differently.

A mostly unscheduled calendar, slow mornings and offline days baked in every few weeks.

I still feel guilty every other day if i’m not as productive as I’d like, but i’m more accepting of it now.

Recently I asked our Art of Mondays community if they ever feel the same. We meet once a month to share ideas and feedback, and they’re all experienced entrepreneurs who care about balance too.

When we spoke, 2 things became clear:

1. Almost everyone suffers from it
2. There is a way to overcome it

But not how you might think.

Just like your muscles need time in rest to recover, so does your mind. You come back stronger. Focused. Self-reflected. More effective.

The magic is creating discipline not in your work time, but in your leisure time.

In case you’re high on coffee and didn’t quite catch that… The quality of your leisure predicts the quality of your work.

…But this doesn’t solve the guilt issue. So i’ll leave you with the words of one of our members, Noah:

“The guilt is… good.

Let it live. Let it drive you. Let it create the feeling that you won’t ever achieve the things you want to achieve if you don’t put in the work today.”

Rather than seeing it as bad and controlling, accept it. Change your relationship with guilt.

Whatever you’re doing this weekend, I hope you’re feeling guilty and stoked. It’s what got me off my lazy ass at 4:09pm on a Saturday to write this Journal Entry for you.

Big love,

Jai

In your (well-prioritised) leisure time, here are a few things you can explore:

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